Arrange a rack in middle of oven and heat to 425°F.
Position an acorn squash on its side. Trim off both ends with a large, sturdy knife. Stand squash upright on a flat end and cut in half lengthwise. Using a spoon, scrape out seeds and any stringy bits. Cut each half into 4 quarters. Place wedges upright, skin side down, in a baking dish or on a rimmed baking sheet. Drizzle with 2 tablespoons olive oil, 1 tablespoon honey, 1 teaspoon salt, and several grinds of pepper.
Roast squash until tender and caramelized at the edges, 40 to 45 minutes.
Heat a large skillet over medium heat. Add half of the salami slices to the pan in a single layer and cook until they curl and are lightly browned, 1 to 2 minutes. Flip slices and cook until browned on the other side, about 1 minute more. Transfer salami to a paper towel–lined plate. Repeat with the remaining salami.
Add 2 tablespoons olive oil to skillet and heat until shimmering. Add sage leaves and cook until crisp and lightly browned, about 30 seconds. Use tongs to flip leaves and cook until crisp on the other side, about 30 seconds more. Transfer leaves to paper towel–lined plate.
Once salami and sage are cool enough to handle, break into small pieces and place in a medium bowl. Remove rind from Gouda and crumble into small pieces with fork tines or a cheese knife, then add to bowl. Add parsley, garlic, sherry vinegar, and remaining tablespoon olive oil. Toss to combine.
Once squash is roasted, cool for a few minutes, then transfer wedges to a serving platter. Spoon cheese mixture over wedges and drizzle with the remaining 2 teaspoons honey.
